WISETRACK COLLECTIVE
THE ADVANTAGE
by Mike Wystrach
Issue #43  |  October 28, 2026
THIS WEEK'S THROUGH-LINE
Put in the years that are not glamorous. Then walk up and introduce yourself.

Welcome Note

Thanks for reading the forty-third issue of The Advantage. This one is brought to you by Proppel. Details on Proppel and the discount for Advantage readers are at the end of the newsletter.

Midland has a No. 1 country album, a six-times Platinum debut single in "Drinkin' Problem," two Grammy nominations and an ACM Award. Right now they are up for Vocal Group of the Year at the CMA Awards, and their new album, Stages, is out.

My twin brother Mark started the band with Jess Carson and Cameron Duddy in 2014. He was 34. They went broke before they got signed. If you think you are too late to start, read this one.

The Practical Edge comes from the Grammys, where I spent every commercial break embarrassed for my brother.

If you are a founder doing $1 million to $40 million in sales and thinking about raising, reach out to us at Cutting Horse. Whether you want an investor or just advice from people who have been in your seat, we are glad to talk.

Let's get into it.

WORTH WATCHING:

Broke Before They Signed

Midland on The Advantage with Mike Wystrach

The Advantage · Mike Wystrach × Midland · 68 min

This week I sat down with Midland: Mark Wystrach, Jess Carson and Cameron Duddy, in their dressing room at the Garden in Boston.

Mark is my twin brother, and he is also one of my best friends. We have gone through most of life together. We both became dads in our 40s, two weeks apart, and our careers took off on roughly the same timeline.

Their new album, Stages, is the one I keep going back to. I love it. The songs feel real, and it sounds like the true country they started with. Dean Dillon wrote "Marlboro Man," and they shot the video in Sonoita, our hometown, in a ranch truck Mark bought off the ranch it was left on.

WHAT I LOVED ABOUT IT:

The overnight success took 16 years. Mark counts from his first live gig at 20.

In 2014 they recorded for ten days at the Sonic Ranch studio in Texas. Cameron went to film it and came back the bass player. Then they went all in. I could not say much. I was knee deep in Freshly, living with Carter in a shitty place.

For close to two years there was no record deal. They paid their own way between Texas and Nashville and played Poodie's for beer money. Cameron had a mortgage, went completely broke, and called their manager, Matt Graham, right before Christmas to ask for help.

I saw them then at the Mercury Lounge in New York, a showcase for the labels. Maybe 15 people, mostly friends from LA. I bought the pizza after because I was the least broke of the broke people.

THE LINE THAT STUCK
"They say burn the lifeboats. But I always kind of felt like even if the lifeboat was burned, I'd swim back. I always find a way."

Cameron Duddy

He moved to Texas because it was the only place he could afford a house.

MY 20-SECOND RECAP
if you do not have the full 68 minutes

→Send the product instead of a pitch. They had no inroads in Nashville, so Cameron shot a video for "14 Gears" and they sent that. Mark: "It was our product. That's what we were selling."

→A hit is not a paycheck. The money is in touring, merch and placements. Mark calls touring "the most dangerous and the hardest part."

→Plan for the plateau. Mark compares music to golf. You get to a level, you stall, you learn the next skill. "That's not sexy. It's not glamorous."

→Do not put your name on something you would not drink. They spent three and a half years tasting batches in Mexico before Insolito went to market.

PRO MOVE

Figure out what your "14 Gears" video is. Make it, and send it to one person this week.

Subscribe to keep reading

This content is free, but you must be subscribed to The Advantage to continue reading.

Already a subscriber?Sign in.Not now